Sodium hydride → HCID 57826339, compound

HRID 1665853Notes

Reaction equation

HRID 1665853 reaction equation
[H-].[Na+].C([CH:5]([O:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)#N.[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1>O1CCCC1.C(OCC)(=O)C.O>[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([C:27](=[O:28])[CH:5]([O:12][C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 312444-MethoxybenzaldehydeHCID 57826353HCID 57826353, compound

Product 1

HCID 57826339HCID 57826339, compoundYield 62.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium hydride (0.27 g, 6.72 mmol) in 10 mL of tetrahydrofuran was slowly added benzoic acid cyano-pyridin-3-yl-methyl ester (1.24 g, 5.61 mmol) prepared in Step 1 at 0° C. After addition was complete, the reaction solution was elevated to room temperature and stirred for 3 hours. Thereafter, 4-methoxybenzaldehyde (0.84 mL, 6.72 mmol) was additionally added to the resulting solution which was then stirred for 3 hours. After the reaction was complete, the reaction materials was diluted with 50 mL of ethyl acetate and 50 mL of water to dissolve salts, followed by separation of layers. The obtained organic layer was successively washed twice with 50 mL of a brine solution. The organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure and purified by silica gel column chromatography, to give 1.21 g (yield: 60%) of benzoic acid 2-(4-methoxy-phenyl)-2-oxo-1-pyridin-3-yl-ethyl ester of the following formula.

Workup

  1. customat 0° C
  2. additionAfter addition
  3. customwas elevated to room temperature
  4. stirringwas then stirred for 3 hours
  5. dissolutionto dissolve salts
  6. customfollowed by separation of layers
  7. washThe obtained organic layer was successively washed twice with 50 mL of a brine solution
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-21aee9539871481bbc19245eaee3f2f9
Source dataset
uspto-grants-2011_10
Patent number
US08039634B2

Reaction notes

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